Through the analysis of the selected works of great Dubrovnik and Croatian baroque writer Ivan Gundulić, the attention is drawn to the importance of the time context in which he lived and created. We explore the connection between the actual circumstances and events that marked that age(the first quarter of the 17. century) and Gundulić's imaginary world represented in the three of his most important pieces. The aim of the research is to determine which historical processes served as motive and inspiration, and which spiritual values were the moral basis for the writing of his works. Gundulić is presented as a writer of universal themes and as an author whose works are at the culprit of European baroque literature. Gundulić touches two great baroque themes: freedom and transiety.His main literaryworks,“Dubravka”, “Osman” and “Tears of Prodigal Son”, created in the later period of his literary career represent the highest form of baroque literary expressionas well as being masterpieces of Croatian literature in general. Selected works of Ivan Gundulić are approached through the context of their creation. Before the piece is analyzed, historical background is exposed as to determine specific political, economic, religious, and social conditions of Gundulić’s era Dubrovnik that might have influenced him. Ivan Gundulić represents a man of his time, who lives, thinks, and writes within the baroque mindset, social and moral values of catholic counter-reformation and the identity concept of early panslavism (called “slovinism” by the contemporaries). Special insight will be made to the context of seemingly contrasted political ideas on the relationship between Dubrovnik and the Ottoman Empire that in the first half of the 17. century created division between the Dubrovnik patricians.